A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1, 1-dioxides. Issue 40 (3rd October 2019)

• Record Type: Journal Article
• Authors: Reed, Carson W.; Lindsley, Craig W.
• Is Part Of: Tetrahedron letters. Volume 60:Issue 40(2019)
• Publication Date: 2019-10-03
• Subjects: Thiomorpholine -- Thiomorpholine 1, 1-dioxide -- Enantioselective -- Organocatalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151104
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: First enantioselective methodology for chiral, C2-subsituted thiomorpholines. Rapid access to chiral thiomorpholine 1, 1-dioxides. Control of stereochemistry based on organocatalyst employed. General protocol affording high % ee. Abstract: In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1, 1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of C2-functionalized thiomorpholines and thiomorpholine 1, 1-dioxides.